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North to Alaska, a Travel Guide: Part 1—Prep and Land(Tour)ing

By Derek May:

Alaska — Photo by Anne Trominski

There are many ways to reach our 49th U.S. state: plane, train, car, dogsled. There are even more reasons to visit: beautiful scenery, unique animal life, polar bear plunges, syrup. For my wife and I, it was a long-delayed honeymoon by cruise ship. Now, don’t get too nervous, I concede that few people want to read an article simply detailing our romantic vacation, so instead I’ll try to focus this piece more as introduction, recommendation, and occasionally cautionary warning for potential travelers interested in making their own way up north at a future date.

That being said, I’ll offer a bit more context for this trip. I’d never been to Alaska, but my wife had. It had always been a bucket-list destination for me, and after years of hearing her adoringly describe her previous adventure, it felt like the perfect place to honeymoon—eventually. As with most things, the pandemic ground our post-nuptial plans to a screeching halt. But in the end, that was ok, because the three-year interval allowed us more time to save and plan for this trip.

In Part 1 here I’m going to concentrate on the prep prior to leaving and the land portion of the tour. In Part 2, we’ll talk more about the cruise and its port destinations.


There are a lot of ways to do Alaska. On our trip, we encountered young couples in rental cars winging it and retirees leisurely bounding through in giant RVs. But most people seem to do what we did, which is to cruise. This was only my second cruise experience, so I’m no expert, but I think that also gives me some insight to advise fellow novices on expectations.

When it comes to Alaskan cruises, there are plenty of options. We’d taken Royal Caribbean on my first cruise in the Gulf of Mexico and thoroughly enjoyed it—except for the hurricanes. I have a fairly sensitive stomach when it comes to motion, so if you do too, you might be hesitant to trap yourself on a hulking ship for a week. I was assured these vessels are so large, with the latest stabilizing technology, that you can’t feel a thing. That is mostly true. Unless you’re traveling between the parallel paths of two summer hurricanes like we did in the Caribbean. In Alaska, however, you stick close to the coast, and thus calmer waters. The only time we could really feel the motion was at higher speeds, and even then I felt ok aside from some minor wooziness. So as someone sharing those concerns, I feel confident saying you’ll be fine and don’t let the waves deter you.

Alaska — Photo by Derek May

After a bit of research and soliciting recommendations, we decided to cruise with Princess. They have a good record in Alaska, lots of options, and it’s a bit of a calmer atmosphere than say the raucous family vibes of Carnival. Of course, that also depends on the time of year. In her first trip, my wife had gone at the very end of the Alaskan tour “season,” which was late September. This time, for various reasons, we decided to go at the very start in early May. Post-trip we discussed the pros and cons of each period:

Going in May, the weather is still cool but warming. There’s still snow, but it’s on its way out, and there’s already a budding of green all around you. With things just gearing up, there aren’t quite as many tourists (relatively speaking), but that also means most of the staff are new and still learning, the tourism machine isn’t quite oiled, and some shops aren’t even open for business yet.

Going in September, it’s starting to get colder, and you may encounter rougher weather spoiling some views. Most of the families are back home and kids are in school, so the numbers are down. In fact, everything is winding down, as businesses prepare to board up for the winter (literally: all shops are emptied and all windows and entrances are sealed), but that means there are plenty of deals to be made should you like to haggle.

Obviously, anything and everything in between goes, so it’s really up to you as to when is best.

Alaska — Photo by Derek May

As far as booking, we have a travel agent friend specializing in cruises, so we used her to customize our trip. While it may have cost a bit more, it might have been worth it, since the Princess website is not the best. It times out or crashes a lot, can be difficult to navigate, and can feel a bit overwhelming with choices and packages that can be hard to distinguish. And I’ll say this right off the bat:

Princess seems to be fantastic at the overall, general experience; where they get lost is in the details.

It can be very difficult to suss out specifics or glean particulars, so it can be helpful to have an agent to guide you.

For our Caribbean cruise, we were really just at sea or stopping at ports, where we’d book an excursion or two for the day. But with Alaska, you really need to spend as much time off the ship and in the interior as you can, and thus I highly recommend adding the land tour to supplement the cruise itself. In most cases, as in ours, that really means a side trip to Denali National Park. This can be added either at the beginning or end of the cruise and is quite honestly a must.

As a final note, if you’re like me and prefer to have everything locked in and ready to go before you leave, you might have to reset expectations. As I said, Princess has a details problem (most of the time easily correctable but for a few wording or programming adjustments), so you might not have all the information you’d expect.

You’ll also need to download their app, which has a lot but not a comprehensive amount of info.

And make sure not only to have everyone in your party download it but that each person has their own account through it (this became an issue for us, more later). You’ll also want to check in much earlier on the app or website than you might think, since you’ll need to enter a wealth of data from passport scans (yes, even though it’s Alaska, you may venture into Canada depending on your trip, so have it up to date and ready) to identification pics. You’ll also need to have your “medallion” sent to you, which takes a few weeks (that deadline is not clearly given up front). If you miss the deadline (as we did), you can get your medallion later, but be warned.


We all know how planes work, so no need to harp on this other than to say be extra careful on your luggage weight. My wife’s bag was 4 measly pounds over, which cost us $100 extra. Coming back, we simply checked a third bag for $35. The nickel and diming is ridiculous.

Arriving in Alaska — Photo by Anne Trominski

You can start your Alaska trip in a number of places: Seattle, Vancouver, etc. We opted to begin in Anchorage, do the Denali land tour, board the ship in Whittier, and disembark in Vancouver, from which we’d fly home. You can adjust your durations however you like but take some time to think it through if you’re concerned about cost. Our original recommended schedule made Anchorage merely a stopover, and we later (though still well in advance) decided we wanted an extra day to explore the city. It was the right call, but that extra night added to the same hotel was a somewhat tricky and costly booking. We weren’t even sure if we we’d be able to get our originally included transfer from the airport to the hotel, but fortunately they had room on the shuttle and allowed us to ride. A plus on the Princess side for that one.


Alaska’s largest city, but you might not believe it. A lovely seaside town, you can easily walk all of downtown quickly and easily. Our accommodation was the grand ole Hotel Captain Cook, an elegant, even luxurious, locale perfectly situated in the heart of the city. It seems to be the go-to for tour groups, particularly Princess, and thus you might not feel the cost as its likely included in your package, but if you add on a night like we did, you’ll notice just how stately it is. Still, it’s an absolutely lovely place, with spacious rooms, nice views (particularly from the Crow’s Nest restaurant and bar on the top floor), and delicious dining (which includes reindeer sausage at breakfast).

Downtown Anchorage, as seen from the Hotel Captain Cook — Photo by Anne Trominski

While you may not need more than an afternoon to walk downtown, if you want to really see anything you’ll need a full day. A lot of shops close by 5 p.m., so you might miss most depending on your arrival time. There are no shortage of great dining options within walking distance, but I’d highly recommend the Glacier Brewhouse (amazing food!) and 49th State Brewing (elevated bar food), but be sure to get to the latter early as it is enormously popular. Speaking of: Snow City Café (just around the corner from the Captain Cook) seems to be THE go-to breakfast place, but either get there early in the morning or prepare to wait.

We’d originally booked a city trolley tour through Princess, but it was mysteriously cancelled. And I do mean “mysterious.” In another example of lack of detail, a sudden and inexplicable refund appeared in our account one day with no other notification or email. It took us a few weeks of messages with our agent to figure out that it was this cancellation. That resolved, we ended up booking our own through Tripadvisor.

Anchorage Downtown Visitor's Center — Photo by Derek May

The tour met at the downtown Visitor’s Center, a lovely little log cabin nestled between souvenir shops just a few blocks from the hotel. Our amazing guide, Donna, was typical Alaskan in that she was a transplant from “the lower 48” (a phrase you’ll hear constantly) who simply never left. In fact, the permanent population throughout Alaska is surprisingly small outside the tourist season. The vast majority of people we met were like our porter at the hotel, a young man (amazingly from our same San Antonio neighborhood) who comes up each summer to work like mad before heading back south. Between wages, tips, and multiple gigs, a person can apparently make a year’s salary in just a few months. Not a bad deal, especially given the Texas summer heat!

Female moose — Photo by Derek May

Our tour hit all the highlights and gave us a nice feel for the city outside downtown. It was in Earthquake Park—site of the 1964 quake that changes magnitude depending on who is telling the story—that we got our first and best view of a full-grown moose! We also stopped at the Ulu Factory, which if not included on a tour you can still walk to (it looks

Ulu Factory emloyee demonstrating use of an ulu — Photo by Derek May

farther on the map than it really is). The shop makes these traditional u-shaped carving knives in-house, and you can get one with a plain handle or made of antler or bone with a scrimshaw (beautiful traditional etching), and they even come in different shapes. You’ll find these amazing, culturally unique tools literally everywhere in Alaska, but few are of substantial quality or locally made (many made in China). So if you want to be sure you got something a little more authentic and, believe-it-or-not, cheaper, grab yours here. Just make sure to check it in your luggage (don’t try to carry it on!).

Other highlights include the bush pilot airport on Lake Hood, the Cook Inlet, and a few

Smoked salmon and reindeer sausage — Photo by Derek May

tourist traps (which were still fun). Our tour was supposed to include a tasting of local smoked salmon and reindeer sausage, which I’d really been looking forward to, but those stores were closed Saturdays (so, why have that tour available on Saturdays to begin with??). Luckily, Donna avoided potential disaster and was prepared by having bought (with her own money) samples of these delights at the market the day before to share with us, along with some homemade jellies. It was all divine and really shows how a great guide can save the day and her company’s risk of a bad review. Lastly, check out the Anchorage Market, a local open-air craft bazaar relocated to the heart of downtown, featuring local artists, craftspeople, and food.


Photo by Anne Trominski

The trip from Anchorage to Denali occurred by bus and took about 5.5 hours. Yes, that’s a long time to sit, but it went quickly due to the spectacular views along the way and our excellent driver/guide, who would regularly expound on various points of interest (look, a bald eagle!). At one rest stop, we got a perfect impression of what the winters are like when we saw snow still packed 3 feet high, covering several picnic tables. A few “brave” souls tried to walk through it and instantly regretted it.

To stay “at Denali” is really a misnomer. The mountain itself is isolated, truly accessible only by helicopter. What people really mean is that you’re staying either beside the national park or in the town of Healy a few miles away. The Denali Princess Wilderness Lodge is a resort complex just outside the park, open to all but really reserved for cruise and tour guests such as us. There are a handful of other options (such as the McKinley Chalet Resort), but the area seems mostly catered to the Princess Lodge.

Denali Princess Wilderness Lodge, main building — Photo by Derek May

The lodge consists of a main reception hall where you access the front desk and get picked up/dropped off for your tours, including catching the regular shuttle to and from the national park. There is a small snack shop on the lower level, but most of the action happens beyond this building. Rooms are located within several structures spanning the complex, interspersed with the handful of overpriced souvenir shops and the on-site dining options. If you’re at the beginning of the year like we were, these will likely be your only options, as the affectionately titled “Glitter Gulch” of shops and eateries directly across the street from the lodge were predominantly still closed at this time. But most of the restaurants on campus are excellent—the exception being Lynx Creek Pizza, which was slow and frankly terrible.

"Glitter Gulch" stretch of shops directly across from the Denali Princess Lodge — Photo by Derek May

Nice as the lodge may be, you don’t want to spend your time there—you want to get out into nature. Our first foray was a small hiking tour up a nearby hilly ridge. With only our guides, Joseph and Johan, and one other couple, it was an intimate and leisurely ascent. These hikes can be catered to various abilities, and I highly recommend taking one, particularly as Joseph was so knowledgeable about the surrounding flora and fauna. I learned Alaska has no snakes (BIG WIN for me!) and learned to identify certain native medicinal growths among the trees such as chaga and the proper way to harvest it.

Hiking view — Photo by Derek May
First-nations speaker — Photo by Derek May

You can travel into the national park itself using the free lodge shuttle that runs every 15 minutes (but be warned, while it stops at multiple locations going in, going back is an express, so plan your return carefully in order not to get stuck—he says from experience). Alternatively, you can schedule a guided Natural History tour, which includes several highlights, a driver’s narration, and a brief talk with some local natives. This was really interesting and our first true delve into the first-nation culture. While all too brief, it was still well worth the trip.

Inside Denali National Park — Photo by Derek May
ATV tour — Photo by Derek May

You can also get out into the bush with several adventures ranging from canoeing to

covered wagons. We opted for an ATV adventure from the well-known Black Diamond company. While fun zipping around on the four-wheeled machine, it was a little disorganized from the start and lacked adequate preparation (you know, like instructions on how to drive the things), so not sure I can truly recommend them.

But when it comes to the big guy, you’ll either need to get creative or rely on luck. The mountain of Denali (formerly known as Mt. McKinley, named for a man who never even visited Alaska) is the highest peak in North America, and it knows it. At 20,000 ft, it is so big it creates its own weather system.

Stop and digest that for a second.

What this means for visitors is that this behemoth tends to shroud itself in clouds most of the time, leading to the ever-present reminder that only 30% of tourists actually get to see it! If you’re not lucky enough to catch a glimpse as it decides to peek out, you can do what we did and take a flightseeing tour to and around the mountain.

Denali Mountain, taken from the air — Photo by Anne Trominski

As we left in the morning for the Denali Air landing strip a few miles from the lodge, the

Glacier tracks near Denali Mountain — Photo by Anne Trominski

mountain was completely covered in grey clouds. But we were assured that the weather at the location itself was quite pleasant, and they were spot on. Nothing but clear blue skies surrounded the massive peaks, allowing us to witness pure white snow as far as the eye could see and as well as the railroad-like parallel tracks of glaciers carving up the valleys. Our pilot, Daniel, was masterful, giving us the smoothest ride I’ve ever had in a tiny 8-person propeller plane. As noted, I can get motion sickness, but that was a non-issue here, though if you have issues with claustrophobia you may reconsider. Otherwise, this was the best and most amazing way to see Denali and absolutely worth every penny.


After two and half days at Denali, it was time to depart. Honestly, you could easily spend a week in the area, but I’d recommend at least a few days. The scenery is breathtaking, the opportunities to venture out numerous, and the wildlife abundant. All a nature-lover’s dream, and you need to give yourself ample time to immerse yourself. If you add this land tour to your package (which I can’t encourage strongly enough), make sure to take full advantage.

Some people we met were coming from or leaving to Fairbanks, a few hours from Denali. As my wife who’d visited before testifies, it’s a small town seeable in a day but boasts some scenic views, especially of the river, and includes a wonderful museum. Completionists will likely not be disappointed in a visit, but if you can’t or choose not to include this city, you probably won’t miss it.

Glass Dome Train from Denali to Whittier — Photo by Anne Trominski

The train out of Denali is located within the national park, requiring a brief bus ride from the lodge. Your assigned car is double deckered, with the lower level containing your particular car’s kitchen, dining area, and bathrooms (all far more spacious than you’d expect). The upper level is generally two columns of paired seating (we were fortunate to have a table up front to ourselves) with a lovely arched glass roof allowing expansive views, immersing you in the surrounding countryside. Though the 9-hour ride may sound daunting, it’s never dull, as the scenery constantly changes around you and the opportunity to spot an elusive bald eagle, moose, bear, or other creature abounds. If you get a good narrator for your car, they can keep you riveted with commentary and insights as

Denali, as seen from train — Photo by Anne Trominski

you go. We truly lucked out in Dillon, a young transplant from Oregon who was funny, witty, and constantly moving to stay on top of any planned or spontaneous point of interest. In particular, he was the first to anticipate our ground-level views of Denali as it cleared its cloud cover on several occasions to give us spectacular sightings of the big fella (and officially inducting everyone into the 30% Club). We knew he was special when the cars around us failed to jump up to see it until Dillon ran over to kindly scold their guide to task.

As you arrive at Whittier in the early evening, you likely won’t see much of the town other than glimpses from the port. While the porters do their best to keep things organized, people being people eschew lines for a mad scrum into the security terminal prior to boarding, so prepare for a certain amount of chaos. But really, getting through security isn’t much different than that for boarding a plane, so expect a similar process and bear it as such.

The Grand Princess in Whittier harbor — Photo by Anne Trominski

And as we now prepare to take our first steps aboard ship, I’ll pause here to give you a rest and prepare you for Part 2, where we’ll discuss expectations at sea and your trip south.

All aboard!


Derek May, of San Antonio, TX, is Editor-in-Chief and occasional writer for Flapper Press. He has written nearly 50 movie reviews for and completed 13 original feature film and television screenplays, many of which have been winners or finalists in such prestigious competitions as the Walt Disney and Nicholl Fellowships, the Austin Film Festival, and the Creative World Awards. He served as a judge for 10 years for the Austin Film Festival and Texas Film Institute screenplay competitions. His latest project has been the highly acclaimed stop-motion animation fan series Highlander: Veritas, which released its second season in July 2022.

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